US3312742A - Process for producing mono-oxonation products of cyclic dimers and trimers of butadiee-(1, 3) - Google Patents
Process for producing mono-oxonation products of cyclic dimers and trimers of butadiee-(1, 3) Download PDFInfo
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- US3312742A US3312742A US394600A US39460064A US3312742A US 3312742 A US3312742 A US 3312742A US 394600 A US394600 A US 394600A US 39460064 A US39460064 A US 39460064A US 3312742 A US3312742 A US 3312742A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/184—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring to a carbon atom of a non-condensed ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
- C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Definitions
- the present invention relates to a process for the production of mono-oxonation products of cyclic dimers and trimers of but'adiene-( 1,3). More particularly, it relates to the production of such dimers and trimers by the action of carbon monoxide and hydrogen in the presence of catalysts comprising mixtures of palladium or cobalt compounds or of finely divided palladium and specially prepared hydrogenation catalysts.
- Cyclic trimers of butadiene such as cyclododecatriene- (1,5,9), have previously been reacted with carbon monoxide and hydrogen under conditions suitable for 0x0- synthesis.
- This method produced a mixture of mono-, di-, and tri-hydroxymethyl-cyclododecanes, the principal product being the di-hydroxymethyl-cyclododecane produced in a yield of 45%.
- this previously known method it has not been possible to confine the reaction to the mono-stage, even by carrying out the reaction in such a manner as to reduce the yield.
- Suitable cobalt catalysts for carrying out the process of the present invention are described in Fort Whitneye der Chemischen Anlagen, vol. 2, page 323 (1951), and include such carbonyl compounds as dicobalt octacarbonyl.
- Suitable palladium compounds include palladium halides such as palladium chloride, palladium bromide, and palladium deposited on charcoal.
- Hydrogenation catalysts stable in the presence of carbon monoxide which are suitable for use in the process of the present invention include: copper/ chromium oxidecontaining catalysts such 'as the compounds referred to as Adkins catalysts in Neuere Methoden der Preparativen Organischen Chemie, vol. 1 (1944), on pages 117- 123 (Verlag Chemie GmbH). Platinum and the so-called Grundmann-Kontakt, a silver/zinc/chromium oxide catalyst are also suitable (see Table 4 and method of preparation given thereunder in Angewandt Chemie, vol. 62, 560 (1950).
- a mixed catalyst suitable for the mono-oxidation of cyclododecatriene-(1,5,9) and cyclooctadiene-(1,5) can be produced by simple mixing of cobalt or palladium catalysts and the carbon monoxide-resistant addition.
- dicobalt octacarbonyl use can be made also of cobalt salts of fatty acids, and particularly of the higher fatty acids, in the presence of acid binding agents such as pyridine o-r quinoline. These cobalt salts under the oxonating conditions produce the effective cobalt catalyst.
- the catalyst is used in amounts ranging from 0.1 to 5%, and preferably from 0.2 to 2.5%, by weight of cyclododecatriene-( 1,3,5) or the cyclooctadiene-(1,5).
- the ratio by weight of the cobalt catalyst or palladium catalysts to the carbon monoxide-resistant addition is :05 to 1:1, and preferably 5: 1.
- the atomic ratio of copper to chro- 3,3 12,742 Patented Apr. 4, 1967 mium can be 10:2 to 2: 10.
- An especially suitable catalyst mixture consists of:
- the carbon monoxiderhydrogen ratio necessary for I mono-oxonation ranges from 120.75 to 1:3, and preferably from 1:1 to 1:2.
- the process can be carried out at pressures ranging from 50 to 500 atms. preferably from 150 to 300 atms.
- Suitable temperatures for the production of formylcyclododecane are from to 250 C., and preferably from to C., and from to 170 C. for the production of hydroxymethyl-cyclododecane. At about C. the hydroxymethyl-cyclododecane is the principal product, being produced in yields in excess of 60%.
- cyclo-dodecatriene as the starting material, symmetrical dicyclododecyldimethyl ether is obtained as a by-product. If to the ether thus produced an equivalent amount of the previously prepared hydroxymethyl-cyclododecane is added, then a yield of more than 90% of the mono-oxidation product will be obtained from the cyclododecatriene. Similar results are obtained when cyclooctadiene-( 1,5) is used as the starting material.
- the process can be carried out in the presence of inert solvents, such as for example, pentane, cyclohexane, or petroleum ether.
- inert solvents such as for example, pentane, cyclohexane, or petroleum ether.
- the mono-oxonation products obtained from cyclododecatriene and cyclo-octadiene are suitable starting materials for the synthesis of synthetic plastics and adjuvants therefor, and for other organic syntheses.
- Adkins catalyst produced by mixing 50.5 g. of Cu(NO .3H O in 54 g. of water with 15.7 g. of Na Cr O in 20 g. of Water, and 20 g. of 25% ammonia solution, filtering with suction, washing, and drying at 320 to 330 C.).
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Cyclododecane and cyclododecene are obtained from 1,5,9-cyclododecatriene and ciscyclooctane from 1,5-cyclooctadiene, as by-products in reaction with CO + H2 in presence of catalysts comprising compounds of Co-Cu-Cr or Co-Ag-Zn-Ca-Cr.ALSO:Cyclododecylmethanol and cyclooctylmethanol are prepared from 1,5,9-cyclododecatriene and 1,5-cyclooctadiene respectively, by reaction with CO + H2 in presence of a catalyst mixture of (a) a Co or Pd compound or finely divided Pd and (b) as a CO-inert hydrogenation component, Cu/Cr oxide, Pt or Ag/Zn/Cr oxide. Specified by-products are formyldodecane, formyloctane, bis-(dodecylmethyl) ether and bis-(octylmethyl) ether.ALSO:Catalysts for oxo-synthesis (see Division C2) comprise (a) a Co or Pd composed or finely-divided Pd and (b) as a CO-inert hydrogenation component, Cu/Cr oxide, Pt or Ag/Zn/Cr oxide. Specified catalysts comprise (1) Co2 (CO)8 + a component precipitated from Cu (NO3)2 and Na2Cr2O7; (2) Co2(CO)8 + a component precipitated from Ag, Ca and Zn nitrates and (NH4)2 Cr2O7; and (3) as in (1) but substituting Co acetate + pyridine for Co2 (CO)8.
Description
United States Patent 7 Claims. at. 260-598) The present invention relates to a process for the production of mono-oxonation products of cyclic dimers and trimers of but'adiene-( 1,3). More particularly, it relates to the production of such dimers and trimers by the action of carbon monoxide and hydrogen in the presence of catalysts comprising mixtures of palladium or cobalt compounds or of finely divided palladium and specially prepared hydrogenation catalysts.
Cyclic trimers of butadiene, such as cyclododecatriene- (1,5,9), have previously been reacted with carbon monoxide and hydrogen under conditions suitable for 0x0- synthesis. This method produced a mixture of mono-, di-, and tri-hydroxymethyl-cyclododecanes, the principal product being the di-hydroxymethyl-cyclododecane produced in a yield of 45%. By this previously known method, however, it has not been possible to confine the reaction to the mono-stage, even by carrying out the reaction in such a manner as to reduce the yield.
It has now been discovered in accordance with the present invention that primarily mono-oxonation products can be obtained by reacting cyclic dimers and trimers of butadiene-( 1,3) i.e., cyclooctadiene-( 1,5), and cyclododecatriene-(l,5,9) in the presence of special mixed catalysts compirsing a cobalt or palladium compound or finely divided palladium and a hydrogenation catalyst which is stable in the presence of carbon monoxide.
Suitable cobalt catalysts for carrying out the process of the present invention are described in Fortschritte der Chemischen Forschung, vol. 2, page 323 (1951), and include such carbonyl compounds as dicobalt octacarbonyl. Suitable palladium compounds include palladium halides such as palladium chloride, palladium bromide, and palladium deposited on charcoal.
Hydrogenation catalysts stable in the presence of carbon monoxide which are suitable for use in the process of the present invention include: copper/ chromium oxidecontaining catalysts such 'as the compounds referred to as Adkins catalysts in Neuere Methoden der Preparativen Organischen Chemie, vol. 1 (1944), on pages 117- 123 (Verlag Chemie GmbH). Platinum and the so-called Grundmann-Kontakt, a silver/zinc/chromium oxide catalyst are also suitable (see Table 4 and method of preparation given thereunder in Angewandt Chemie, vol. 62, 560 (1950).
A mixed catalyst suitable for the mono-oxidation of cyclododecatriene-(1,5,9) and cyclooctadiene-(1,5) can be produced by simple mixing of cobalt or palladium catalysts and the carbon monoxide-resistant addition. Instead of dicobalt octacarbonyl, use can be made also of cobalt salts of fatty acids, and particularly of the higher fatty acids, in the presence of acid binding agents such as pyridine o-r quinoline. These cobalt salts under the oxonating conditions produce the effective cobalt catalyst. The catalyst is used in amounts ranging from 0.1 to 5%, and preferably from 0.2 to 2.5%, by weight of cyclododecatriene-( 1,3,5) or the cyclooctadiene-(1,5). The ratio by weight of the cobalt catalyst or palladium catalysts to the carbon monoxide-resistant addition is :05 to 1:1, and preferably 5: 1. The atomic ratio of copper to chro- 3,3 12,742 Patented Apr. 4, 1967 mium can be 10:2 to 2: 10. An especially suitable catalyst mixture consists of:
25 g. dicobalt octacarbonyl 5 g. Adkins catalyst produced from:
260 g. cupric nitrate (Cu(NO .3H O) 151 g. ammonium bichromate 31 g. barium nitrate 225 ml. 28% ammonia solution The carbon monoxiderhydrogen ratio necessary for I mono-oxonation ranges from 120.75 to 1:3, and preferably from 1:1 to 1:2. The process can be carried out at pressures ranging from 50 to 500 atms. preferably from 150 to 300 atms.
Suitable temperatures for the production of formylcyclododecane are from to 250 C., and preferably from to C., and from to 170 C. for the production of hydroxymethyl-cyclododecane. At about C. the hydroxymethyl-cyclododecane is the principal product, being produced in yields in excess of 60%. When using cyclo-dodecatriene as the starting material, symmetrical dicyclododecyldimethyl ether is obtained as a by-product. If to the ether thus produced an equivalent amount of the previously prepared hydroxymethyl-cyclododecane is added, then a yield of more than 90% of the mono-oxidation product will be obtained from the cyclododecatriene. Similar results are obtained when cyclooctadiene-( 1,5) is used as the starting material.
If desired, the process can be carried out in the presence of inert solvents, such as for example, pentane, cyclohexane, or petroleum ether.
The mono-oxonation products obtained from cyclododecatriene and cyclo-octadiene are suitable starting materials for the synthesis of synthetic plastics and adjuvants therefor, and for other organic syntheses.
The examples given below 'are for the purpose of illustrating the process of producing mono-oxonation products of dimers and trimers of butadiene-(1,3) and it is to be understood that various modifications and departures from the described procedures will be obvious to one skilled in the art. Any such modifications which do not depart from the concept of the present invention are intended to be included in the appended claims.
EXAMPLE 1 A 5 l. autoclave provided with heating netic agitator was charged with:
jacket and mag- 1500 g. cis-trans-trans-cyclododecatriene-(1,5,9)
25 g. dicobalt octacarbonyl 5 g. Adkins catalyst (produced by mixing 50.5 g. of Cu(NO .3H O in 54 g. of water with 15.7 g. of Na Cr O in 20 g. of Water, and 20 g. of 25% ammonia solution, filtering with suction, washing, and drying at 320 to 330 C.).
(1) A small preliminary fraction consisting essentially of cyclododecane (2) 1135 .g. of hydroxymethyl-cyclododecane (61.9% of the theoretical), B.P. 0.5 IDS-107 C.; M.P. 32-33 C.; n =L4884 (3) 517 g. of symmetrical dicyclododecyldimethyl i) ether (29.4% of'the theoretical); B.P. 0.05 175-178 C., n =l.5O01.
EXAMPLE 2 (1) 411 g. of formylcyclo-dodecane (22.7% of the theoretical) B.P. 0.5 94-96 C., n =L4820 (2) 664 g. of hydroxymethyl-cyclododecane (36.2% of the theoretical) (3) 345 g. symmetrical (19.7% of the theoretical).
The total amounts to 78% of the theoretical monooxidation products.
EXAMPLE 3 In this experiment the following materials were introduced into a liter autoclave and the operation carried out as described in Example 1:
didodecyl-dimethylether 1500 g. cis-trans-trans-cyclododecatriene 25 g. dicobalt octacarbonyl 5 g. Grundmann Kontakt (prepared as described in Angew. Chem. 62, 560 (1950).
After completion of the reaction the reaction product was vacuum distilled and the following fractions obtained:
(1) 99 g. of cyclododecen (6.5% of the theoretical) (2) 1287 g. (70.8% of the theoretical) of a mixture of 70% hydroxymethyl-cyclododecane and 30% of formylcyclododecane n =1.4870
(3) 180 g. of symmetrical dicyclododecyldimethyl ether (10.3% of the theoretical).
EXAMPLE 4 The following materials were placed in a 5 liter autoclave and the reaction carried out-as described in Example 1:
1500 g. cis-trans-trans-cyclododecatriene 35.5 g. cobalt acetate tetrahydrate 23.2 g. pyridine 5 g. Adkins catalyst prepared as in Example 1.
Vacuum distillation of the reaction product gave the following fractions:
267 g. of formyl-cyclododecane (14.7% of the theoretical) d 1163 g. of hydroxy-methyl-cyclododecane (63% of the theoretical).
There was also obtained a higher boiling fraction of unsaturated carboxyl and formyl compounds.
EXAMPLE 5 The followingmaterials were reacted as described in Example 1:
15 00 g. cyclooctad-iene-( 1,5 25 g. dicobalt octacarbonyl 5 g. Adkins catalyst prepared as described in Example 1.
After completion of the reaction, the catalyst was separated by filtration with suction and the filtrate distilled under vacuum with the following results:
1) 270 g. of cis-cyclooctene (17.7% of the theoretical) B.P. 0.5 4649 C., n =1.4680
(2) 1102 g. of formyl-cyclooctane (56.7% of the theoretical B.P. 0.5 7173 C., n =1.4732
(3) 328 g. of residue containing about 30% of hydroxymethyl-cyclooctane and 20% of symmetrical dicyclooctyldimethyl ether.
What is claimed is: 1. Process for the production of mono-oxonation products of cyclic dimers and trimers of 'butadiene-(L3) which comprises: subjecting at least one of said dimers and trimers to treatment with a mixture of carbon monoxide and hydrogen in a ratio of between 1:0.75 and 1:3 at elevated temperatures and pressures in the presence of a mixed catalyst comprising (a) a catalyst selected from the group consisting of cobalt carbonyls, co balt salts of fatty acids with an acid binding agent, palladium halides, and finely divided palladium, and (b) a carbon monoxide-resistant hydrogenation catalyst selected from the group consisting of copper/ chromium oxide catalysts, platinum, and silver/ zinc/ chromium oxide catalysts, wherein the ratio of (a) and (b) is between 10:0.5
and 1:1. 2. The process of claim 1 where in the ratio of (a) to b) is about 5:1.
3. The process of claim 1 wherein the carbon monoxide/hydrogen \ratio is 1:1 to 1:2.
4. The process of claim 1 wherein said treatment is conducted at 50 to 500 atmospheres.
5. The process of claim 1 wherein said treatment is conducted at 150 to 300 atmospheres.
6. The process of claim 1 wherein the treatment is conducted at 250 C.
7. The process of claim 1, wherein the treatment is conducted at -180 C.
References Cited by the Examiner UNITED STATES PATENTS 3,184,432 5/1965 Wilke et al. 2 60598 X LEON ZITVER, Primary Examiner.
R. H. LILES, Assistant Examiner.
Claims (1)
1. PROCESS FOR THE PRODUCTION OF MONO-OXONATION PRODUCTS OF CYCLIC DIMERS AND TRIMERS OF BUTADIENE-(1,3) WHICH COMPRISES: SUBJECTING AT LEAST ONE OF SAID DIMERS AND TRIMERS TO TREATMENT WITH A MIXTURE OF CARBON MONOXIDE AND HYDROGEN IN A RATIO OF BETWEEN 1:0.75 AND 1:3 AT ELEVATED TEMPERATURES AND PRESSURES IN THE PRESENCE OF A MIXED CATALYST COMPRISING (A) A CATALYST SELECTED FROM THE GROUP CONSISTING OF COBALT CARBONYLS, COBALT SALTS OF FATTY ACIDS WITH AN ACID BINDING AGENT, PALLADIUM HALIDES, AND FINELY DIVIDED PALLADIUM, AND (B) A CARBON MONOXIDE-RESISTANT HYDROGENATION CATALYST SELECTED FROM THE GROUP CONSISTING OF COPPER/ CHROMIUM OXIDE CATALYSTS, PLATINUM, AND SILVER/ ZINC/CHROMIUM OXIDE CATALYSTS, WHEREIN THE RATIO OF (A) AND (B) IS BETWEEN 10:0.5 AND 1:1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC31165A DE1211174B (en) | 1963-10-17 | 1963-10-17 | Process for the preparation of monooxation products of the cyclic di- and trimers of butadiene- (1, 3) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3312742A true US3312742A (en) | 1967-04-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US394600A Expired - Lifetime US3312742A (en) | 1963-10-17 | 1964-09-04 | Process for producing mono-oxonation products of cyclic dimers and trimers of butadiee-(1, 3) |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3312742A (en) |
| CH (1) | CH437264A (en) |
| DE (1) | DE1211174B (en) |
| GB (1) | GB1075267A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3378590A (en) * | 1964-05-27 | 1968-04-16 | Toa Nenryo Kogyo Kk | Production of aldehydes and/or alcohols from compound having olefinic double bonds |
| US4251462A (en) * | 1978-09-06 | 1981-02-17 | Bayer Aktiengesellschaft | Aminomethyl cyclododecanes, a process for their production and their use as corrosion inhibitors |
| WO2013126641A1 (en) | 2012-02-24 | 2013-08-29 | Dow Global Technologies Llc | Preparation and use of cyclododecatriene trialdehyde and related compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2928347C2 (en) * | 1979-07-13 | 1981-11-26 | Chemische Werke Hüls AG, 4370 Marl | Aliphatic ethers of hydroxymethylcyclododecane, combinations of substances containing them and their use for the production of fragrance compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184432A (en) * | 1957-10-24 | 1965-05-18 | Studiengesellschaft Kohle Mbh | Process for the production of cyclododecane derivatives |
-
1963
- 1963-10-17 DE DEC31165A patent/DE1211174B/en active Pending
-
1964
- 1964-09-04 US US394600A patent/US3312742A/en not_active Expired - Lifetime
- 1964-10-14 CH CH1333064A patent/CH437264A/en unknown
- 1964-10-16 GB GB42248/64A patent/GB1075267A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184432A (en) * | 1957-10-24 | 1965-05-18 | Studiengesellschaft Kohle Mbh | Process for the production of cyclododecane derivatives |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3378590A (en) * | 1964-05-27 | 1968-04-16 | Toa Nenryo Kogyo Kk | Production of aldehydes and/or alcohols from compound having olefinic double bonds |
| US4251462A (en) * | 1978-09-06 | 1981-02-17 | Bayer Aktiengesellschaft | Aminomethyl cyclododecanes, a process for their production and their use as corrosion inhibitors |
| WO2013126641A1 (en) | 2012-02-24 | 2013-08-29 | Dow Global Technologies Llc | Preparation and use of cyclododecatriene trialdehyde and related compounds |
| US9328193B2 (en) | 2012-02-24 | 2016-05-03 | Dow Global Technologies Llc | Preparation and use of cyclododecatriene trialdehyde and related compounds |
| US9598339B2 (en) | 2012-02-24 | 2017-03-21 | Dow Global Technologies Llc | Preparation and use of cyclododecatriene trialdehyde and related compounds |
| US9656936B1 (en) | 2012-02-24 | 2017-05-23 | Dow Global Technologies Llc | Preparation and use of cyclododecatriene trialdehyde and related compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1075267A (en) | 1967-07-12 |
| DE1211174B (en) | 1966-02-24 |
| CH437264A (en) | 1967-06-15 |
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